CA2128509C - Continuous process for manufacture of lactide polymers with improved purification methods - Google Patents

Continuous process for manufacture of lactide polymers with improved purification methods Download PDF

Info

Publication number: CA2128509C
Authority: CA; Canada
Prior art keywords: lactide; lactic acid; mixture; crude; stream
Prior art date: 1992-01-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002128509A

Other languages

English (en)

French (fr)

Other versions

CA2128509A1 (en

Inventor

Patrick R. Gruber

Eric S. Hall

Jeffrey J. Kolstad

Matthew L. Iwen

Richard D. Benson

Ronald L. Borchardt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Cargill Inc

Original Assignee

Cargill Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-01-24

Filing date

1993-01-22

Publication date

2006-09-19

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27542241&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2128509(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1992-01-24 Priority claimed from US07/825,059 external-priority patent/US5142023A/en

1992-08-07 Priority claimed from US07/927,149 external-priority patent/US5247058A/en

1992-08-07 Priority claimed from US07/926,901 external-priority patent/US5258488A/en

1992-08-24 Priority claimed from US07/935,566 external-priority patent/US5247059A/en

1993-01-22 Application filed by Cargill Inc filed Critical Cargill Inc

1993-08-05 Publication of CA2128509A1 publication Critical patent/CA2128509A1/en

2006-09-19 Application granted granted Critical

2006-09-19 Publication of CA2128509C publication Critical patent/CA2128509C/en

2013-01-22 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 title claims abstract description 430
238000000034 method Methods 0.000 title claims abstract description 107
229920000642 polymer Polymers 0.000 title claims abstract description 92
238000004519 manufacturing process Methods 0.000 title claims description 46
238000000746 purification Methods 0.000 title abstract description 23
238000010924 continuous production Methods 0.000 title abstract description 6
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 551
235000014655 lactic acid Nutrition 0.000 claims abstract description 274
239000004310 lactic acid Substances 0.000 claims abstract description 272
239000003054 catalyst Substances 0.000 claims abstract description 183
229920000747 poly(lactic acid) Polymers 0.000 claims abstract description 163
238000004821 distillation Methods 0.000 claims abstract description 142
239000004626 polylactic acid Substances 0.000 claims abstract description 130
150000002148 esters Chemical class 0.000 claims abstract description 100
230000008569 process Effects 0.000 claims abstract description 93
239000000203 mixture Substances 0.000 claims description 122
238000009835 boiling Methods 0.000 claims description 79
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
230000000694 effects Effects 0.000 claims description 31
JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims description 30
230000005494 condensation Effects 0.000 claims description 25
238000009833 condensation Methods 0.000 claims description 24
JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 claims description 20
239000007787 solid Substances 0.000 claims description 16
125000004122 cyclic group Chemical group 0.000 claims description 14
239000002609 medium Substances 0.000 claims description 14
238000001704 evaporation Methods 0.000 claims description 13
238000001953 recrystallisation Methods 0.000 claims description 13
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
230000008020 evaporation Effects 0.000 claims description 10
239000012736 aqueous medium Substances 0.000 claims description 8
150000002739 metals Chemical class 0.000 claims description 8
238000000638 solvent extraction Methods 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 5
238000009834 vaporization Methods 0.000 claims description 3
230000000737 periodic effect Effects 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims 3
238000006482 condensation reaction Methods 0.000 abstract description 30
239000006227 byproduct Substances 0.000 abstract description 27
239000002253 acid Substances 0.000 abstract description 22
239000000463 material Substances 0.000 description 68
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
238000006243 chemical reaction Methods 0.000 description 51
238000006116 polymerization reaction Methods 0.000 description 50
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 44
239000012535 impurity Substances 0.000 description 42
230000003287 optical effect Effects 0.000 description 32
LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 30
ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 30
229940057867 methyl lactate Drugs 0.000 description 30
239000000047 product Substances 0.000 description 26
239000002904 solvent Substances 0.000 description 26
239000007788 liquid Substances 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(II) oxide Inorganic materials [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 24
230000007246 mechanism Effects 0.000 description 23
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 22
229940116333 ethyl lactate Drugs 0.000 description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
238000012546 transfer Methods 0.000 description 22
230000008901 benefit Effects 0.000 description 20
230000006340 racemization Effects 0.000 description 20
238000010438 heat treatment Methods 0.000 description 19
239000000539 dimer Substances 0.000 description 14
238000002474 experimental method Methods 0.000 description 14
230000003068 static effect Effects 0.000 description 14
-1 cyclic ester Chemical class 0.000 description 13
238000010926 purge Methods 0.000 description 13
239000012299 nitrogen atmosphere Substances 0.000 description 12
238000013461 design Methods 0.000 description 11
239000012071 phase Substances 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
229920001577 copolymer Polymers 0.000 description 10
230000004044 response Effects 0.000 description 10
238000007142 ring opening reaction Methods 0.000 description 10
239000000126 substance Substances 0.000 description 10
238000007701 flash-distillation Methods 0.000 description 9
239000000178 monomer Substances 0.000 description 9
MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 8
239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
238000012691 depolymerization reaction Methods 0.000 description 8
238000009826 distribution Methods 0.000 description 8
239000012530 fluid Substances 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
238000002156 mixing Methods 0.000 description 8
230000004048 modification Effects 0.000 description 8
238000012986 modification Methods 0.000 description 8
230000000704 physical effect Effects 0.000 description 8
229930182843 D-Lactic acid Natural products 0.000 description 7
JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 7
150000001735 carboxylic acids Chemical class 0.000 description 7
229920001429 chelating resin Polymers 0.000 description 7
229940022769 d- lactic acid Drugs 0.000 description 7
229910014033 C-OH Inorganic materials 0.000 description 6
229910014570 C—OH Inorganic materials 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000005227 gel permeation chromatography Methods 0.000 description 6
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000007086 side reaction Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000011949 solid catalyst Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
239000002699 waste material Substances 0.000 description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 5
229920002988 biodegradable polymer Polymers 0.000 description 5
239000004621 biodegradable polymer Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
230000001627 detrimental effect Effects 0.000 description 5
239000002815 homogeneous catalyst Substances 0.000 description 5
150000007517 lewis acids Chemical class 0.000 description 5
230000036961 partial effect Effects 0.000 description 5
238000012545 processing Methods 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000000356 contaminant Substances 0.000 description 4
PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical compound [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 description 4
238000011084 recovery Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
WBPAQKQBUKYCJS-UHFFFAOYSA-N 2-methylpropyl 2-hydroxypropanoate Chemical compound CC(C)COC(=O)C(C)O WBPAQKQBUKYCJS-UHFFFAOYSA-N 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
229920001730 Moisture cure polyurethane Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229940061720 alpha hydroxy acid Drugs 0.000 description 3
150000001280 alpha hydroxy acids Chemical class 0.000 description 3
125000002091 cationic group Chemical group 0.000 description 3
230000008859 change Effects 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
239000011651 chromium Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000011161 development Methods 0.000 description 3
239000010408 film Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
150000003903 lactic acid esters Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229910021645 metal ion Inorganic materials 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 3
ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000004448 titration Methods 0.000 description 3
230000032258 transport Effects 0.000 description 3
238000010977 unit operation Methods 0.000 description 3
239000012808 vapor phase Substances 0.000 description 3
RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
230000004913 activation Effects 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
239000012620 biological material Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000003750 conditioning effect Effects 0.000 description 2
238000011109 contamination Methods 0.000 description 2
238000012937 correction Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000010586 diagram Methods 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
230000008570 general process Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000011572 manganese Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000010907 mechanical stirring Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
UQGPCEVQKLOLLM-UHFFFAOYSA-N pentaneperoxoic acid Chemical compound CCCCC(=O)OO UQGPCEVQKLOLLM-UHFFFAOYSA-N 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920002959 polymer blend Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000004064 recycling Methods 0.000 description 2
230000011514 reflex Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
229910001887 tin oxide Inorganic materials 0.000 description 2
238000005809 transesterification reaction Methods 0.000 description 2
238000011144 upstream manufacturing Methods 0.000 description 2
239000003643 water by type Substances 0.000 description 2
238000004260 weight control Methods 0.000 description 2
OZZQHCBFUVFZGT-UHFFFAOYSA-N 2-(2-hydroxypropanoyloxy)propanoic acid Chemical compound CC(O)C(=O)OC(C)C(O)=O OZZQHCBFUVFZGT-UHFFFAOYSA-N 0.000 description 1
BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 1
241000132028 Bellis Species 0.000 description 1
241001436672 Bhatia Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229910021556 Chromium(III) chloride Inorganic materials 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000004075 alteration Effects 0.000 description 1
238000000540 analysis of variance Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
PEWNRQODUMGNCG-UHFFFAOYSA-N azanium;1,4-bis(8-methylnonoxy)-1,4-dioxobutane-2-sulfonate Chemical compound [NH4+].CC(C)CCCCCCCOC(=O)CC(S([O-])(=O)=O)C(=O)OCCCCCCCC(C)C PEWNRQODUMGNCG-UHFFFAOYSA-N 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
239000001639 calcium acetate Substances 0.000 description 1
235000011092 calcium acetate Nutrition 0.000 description 1
229960005147 calcium acetate Drugs 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
239000011636 chromium(III) chloride Substances 0.000 description 1
235000007831 chromium(III) chloride Nutrition 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000010961 commercial manufacture process Methods 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000013365 dairy product Nutrition 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
239000000428 dust Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
IGJUMYVLIWBDFK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.CCOC(=O)C(C)O IGJUMYVLIWBDFK-UHFFFAOYSA-N 0.000 description 1
238000013462 factorial design experiment Methods 0.000 description 1
239000011552 falling film Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
238000007726 management method Methods 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
229940071125 manganese acetate Drugs 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
229940127554 medical product Drugs 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
238000012856 packing Methods 0.000 description 1
238000003359 percent control normalization Methods 0.000 description 1
239000003348 petrochemical agent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000011020 pilot scale process Methods 0.000 description 1
229920001432 poly(L-lactide) Polymers 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007151 ring opening polymerisation reaction Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229960004249 sodium acetate Drugs 0.000 description 1
239000011343 solid material Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
238000004457 water analysis Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1
229960000314 zinc acetate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

CA002128509A 1992-01-24 1993-01-22 Continuous process for manufacture of lactide polymers with improved purification methods Expired - Fee Related CA2128509C (en)

Applications Claiming Priority (11)

Application Number	Priority Date	Filing Date	Title
US07/825,059		1992-01-24
US07/825,059 US5142023A (en)	1992-01-24	1992-01-24	Continuous process for manufacture of lactide polymers with controlled optical purity
US07/927,149 US5247058A (en)	1992-01-24	1992-08-07	Continuous process for manufacture of lactide polymers with controlled optical purity
US07/926,901		1992-08-07
US07/927,149		1992-08-07
US07/926,901 US5258488A (en)	1992-01-24	1992-08-07	Continuous process for manufacture of lactide polymers with controlled optical purity
US07/935,059		1992-08-24
US07/935,566 US5247059A (en)	1992-01-24	1992-08-24	Continuous process for the manufacture of a purified lactide from esters of lactic acid
US07/935,059 US5274073A (en)	1992-01-24	1992-08-24	Continuous process for manufacture of a purified lactide
US07/935,566		1992-08-24
PCT/US1993/000568 WO1993015127A1 (en)	1992-01-24	1993-01-22	Continuous process for the manufacture of lactide and lactide polymers

Publications (2)

Publication Number	Publication Date
CA2128509A1 CA2128509A1 (en)	1993-08-05
CA2128509C true CA2128509C (en)	2006-09-19

Family

ID=27542241

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002128509A Expired - Fee Related CA2128509C (en)	1992-01-24	1993-01-22	Continuous process for manufacture of lactide polymers with improved purification methods

Country Status (14)

Country	Link
EP (2)	EP0623153A1 (de)
JP (1)	JP3258324B2 (de)
KR (1)	KR100261850B1 (de)
AT (1)	ATE466897T1 (de)
AU (1)	AU677174B2 (de)
BR (1)	BR9305788A (de)
CA (1)	CA2128509C (de)
DE (1)	DE69334330D1 (de)
ES (1)	ES2345307T3 (de)
FI (1)	FI113661B (de)
MX (1)	MX9300333A (de)
NO (1)	NO309530B1 (de)
NZ (1)	NZ249033A (de)
WO (1)	WO1993015127A1 (de)

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1993
- 1993-01-22 AT AT98203427T patent/ATE466897T1/de not_active IP Right Cessation
- 1993-01-22 EP EP93903632A patent/EP0623153A1/de not_active Ceased
- 1993-01-22 KR KR1019940702555A patent/KR100261850B1/ko not_active Expired - Fee Related
- 1993-01-22 JP JP51333593A patent/JP3258324B2/ja not_active Expired - Fee Related
- 1993-01-22 NZ NZ249033A patent/NZ249033A/en not_active IP Right Cessation
- 1993-01-22 CA CA002128509A patent/CA2128509C/en not_active Expired - Fee Related
- 1993-01-22 WO PCT/US1993/000568 patent/WO1993015127A1/en not_active Ceased
- 1993-01-22 EP EP98203427A patent/EP0893462B1/de not_active Expired - Lifetime
- 1993-01-22 ES ES98203427T patent/ES2345307T3/es not_active Expired - Lifetime
- 1993-01-22 AU AU34821/93A patent/AU677174B2/en not_active Ceased
- 1993-01-22 DE DE69334330T patent/DE69334330D1/de not_active Expired - Lifetime
- 1993-01-22 MX MX9300333A patent/MX9300333A/es unknown
- 1993-01-22 BR BR9305788A patent/BR9305788A/pt not_active IP Right Cessation
1994
- 1994-07-21 NO NO942728A patent/NO309530B1/no not_active IP Right Cessation
- 1994-07-22 FI FI943487A patent/FI113661B/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
KR100261850B1 (ko)	2000-08-01
WO1993015127A1 (en)	1993-08-05
JPH07503490A (ja)	1995-04-13
BR9305788A (pt)	1997-02-18
NO309530B1 (no)	2001-02-12
EP0893462A3 (de)	1999-10-20
NZ249033A (en)	1996-05-28
AU3482193A (en)	1993-09-01
FI943487L (fi)	1994-09-21
FI113661B (fi)	2004-05-31
EP0893462A2 (de)	1999-01-27
FI943487A0 (fi)	1994-07-22
ES2345307T3 (es)	2010-09-20
CA2128509A1 (en)	1993-08-05
AU677174B2 (en)	1997-04-17
JP3258324B2 (ja)	2002-02-18
ATE466897T1 (de)	2010-05-15
MX9300333A (es)	1993-07-01
DE69334330D1 (de)	2010-06-17
EP0623153A1 (de)	1994-11-09
NO942728D0 (no)	1994-07-21
NO942728L (no)	1994-09-23
EP0893462B1 (de)	2010-05-05

Legal Events

Date	Code	Title	Description
2000-01-12	EEER	Examination request
2013-03-05	MKLA	Lapsed	Effective date: 20130122

Publication	Publication Date	Title
CA2128509C (en)	2006-09-19	Continuous process for manufacture of lactide polymers with improved purification methods
US5247059A (en)	1993-09-21	Continuous process for the manufacture of a purified lactide from esters of lactic acid
US5274073A (en)	1993-12-28	Continuous process for manufacture of a purified lactide
US5258488A (en)	1993-11-02	Continuous process for manufacture of lactide polymers with controlled optical purity
US5247058A (en)	1993-09-21	Continuous process for manufacture of lactide polymers with controlled optical purity
US6005067A (en)	1999-12-21	Continuous process for manufacture of lactide polymers with controlled optical purity
CA2173616C (en)	2006-08-29	Continuous process for the manufacture of lactide and lactide polymers
CN103781833B (zh)	2017-02-15	从聚丙交酯回收丙交酯或从聚乙交酯回收乙交酯的方法和装置
EP2406246B1 (de)	2018-08-15	Verfahren zur herstellung von lactid mit recyceln von meso-lactid
JP4672554B2 (ja)	2011-04-20	脂肪族ポリエステルの製造方法
GB2407572A (en)	2005-05-04	Method for the production of polylactide from a solution of lactic acid or one of the derivatives thereof
EP0531462A1 (de)	1993-03-17	Verfahren zur reinigung von cyclischen estern.
EP0641336A1 (de)	1995-03-08	Dünnfilmdepolymerisierung zu dimeren cyclischen estern
US5229528A (en)	1993-07-20	Rapid depolymerization of polyhydroxy acids
JP4994314B2 (ja)	2012-08-08	ラクチド及びポリ乳酸の合成方法及び装置
US20250100991A1 (en)	2025-03-27	Method for processing lactides
US6060622A (en)	2000-05-09	Methods of reproducing lactic acid components by using lactic acid based by-products
US5342969A (en)	1994-08-30	Recovery of hydroxycarboxylic acid values from poly(hydroxycarboxylic acids)
US5268507A (en)	1993-12-07	Preparation of amide derivatives of hydroxy acids
US5264626A (en)	1993-11-23	Rapid depolymerization of polyhydroxy acids
JPH1192475A (ja)	1999-04-06	ラクチドの迅速な製造方法
EP4613742A1 (de)	2025-09-10	Verfahren und anlage zur herstellung einer rohlactidzusammensetzung unter verwendung eines lactidsynthesereaktors mit einer destillationssäule und einem schlaufenreaktor
WO2022139675A1 (en)	2022-06-30	Process for the production of lactide
JPH10287668A (ja)	1998-10-27	乳酸アンモニウムからラクチド及びポリ乳酸を製造する方法
WO2024160884A1 (en)	2024-08-08	Process for producing a polymeso-lactide